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Chiraphos

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(Redirected from 2,3-Bis(diphenylphosphino)butane)
Chiraphos
Names
Preferred IUPAC name rel-bis(diphenylphosphane)
Other names
  • (2S,3S)-(–)-Bis(diphenylphosphino)butane
  • (2R,3R)-(+)-Bis(diphenylphosphino)butane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.152.152 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C28H28P2/c1-23(29(25-15-7-3-8-16-25)26-17-9-4-10-18-26)24(2)30(27-19-11-5-12-20-27)28-21-13-6-14-22-28/h3-24H,1-2H3/t23-,24-/m0/s1Key: FWXAUDSWDBGCMN-ZEQRLZLVSA-N
  • InChI=1/C28H28P2/c1-23(29(25-15-7-3-8-16-25)26-17-9-4-10-18-26)24(2)30(27-19-11-5-12-20-27)28-21-13-6-14-22-28/h3-24H,1-2H3/t23-,24-/m0/s1Key: FWXAUDSWDBGCMN-ZEQRLZLVBA
SMILES
  • P(c1ccccc1)(c2ccccc2)((P(c3ccccc3)c4ccccc4)C)C
Properties
Chemical formula C28H28P2
Molar mass 426.47 g/mol
Appearance White powder
Melting point 104 to 109 °C (219 to 228 °F; 377 to 382 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Chiraphos is a chiral diphosphine employed as a ligand in organometallic chemistry. This bidentate ligand chelates metals via the two phosphine groups. Its name is derived from its description — being both chiral and a phosphine. As a C2-symmetric ligand, chiraphos is available in two enantiomeric forms, S,S and R,R, each with C2 symmetry.

Preparation

Chiraphos is prepared from S,S or R,R-2,3-butanediol, which are derived from commercially available S,S or R,R-tartaric acid; the technique of using cheaply available enantiopure starting materials is known as chiral pool synthesis. The diol is tosylated and then the ditosylate is treated with lithium diphenylphosphide. The ligand was an important demonstration of how the conformation of the chelate ring can affect asymmetric induction by a metal catalyst. Prior to this work, in most chiral phosphines, e.g., DIPAMP, phosphorus was the stereogenic center.

References

  1. Fryzuk, M. D.; Bosnich, B. (1977). "Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation". Journal of the American Chemical Society. 99 (19): 6262–6267. doi:10.1021/ja00461a014. PMID 893889.
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